


Long Time

by supernatural_jackles



Series: Long Time [1]
Category: Supernatural
Genre: AU, Angst, F/M, Implications of a Past Abusive Relationship, Money Problems. A Pinch of Fluff., Self-Doubt, Single Parent AU, daddy!dean, self-hate
Language: English
Status: In-Progress
Published: 2018-12-05
Updated: 2019-01-16
Packaged: 2019-09-07 17:07:55
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 12,198
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16857952
Author URL: https://archiveofourown.org/users/supernatural_jackles/pseuds/supernatural_jackles
Summary: Dean Winchester is a single parent to his six year old daughter, Mary. His daughter brings home her best friend, Ella, who’s mother is running late. He takes her in to wait, not quite able to place where he had seen this  girl before. When she knocks on the door, he finally realizes just where he’s seen the little girl. She’s a spitting image of her mother, Y/N. The girl he fell for many years ago.





	1. Long Time

   Thursday night was going in typical fashion. Dean finished work right on time, headed straight home, making it right on time for his daughter to run off the bus and into his arms, just like she did everyday when she finished school. She was beautiful, absolutely beautiful to him. There wasn’t a single thing that he didn’t love about his daughter. She was the light in his life. His everything and been for six years.

 What was different this time, was another little girl that followed his daughter Mary home. A shy, small girl that kept her distance between Dean and his daughter. Her head cast downwards as she adjusted the straps on her backpack.

 “What’s your name, kiddo?” he asked her, slowly making his way over to the little girl. He wondered if maybe her parents were running late. Either way, he wasn’t going to leave her on her own.

 “Ella,” she muttered. He swore she looked familiar to him. Her small, gorgeous Y/E/C reminded him of someone he used to know. Her hair was pulled up in a half up, half down thing that he’s done to his own daughter many times.

 “Where’s your parents?” he questioned, shaking his head slightly to push the thought out of his mind. Mary walked over to him, placing her hand on his shoulder, something she did to keep close to him, and reassure him that she was right there with him.

 “I think my mommy is still working. She’s only late if she’s still working,” she stated.

 “Alright, where do you live? We can leave a note on your door for your mom so she knows that you’re safe. You can stay with Mary and I until she’s finished work. Is that okay?” The little girl nodded her head. She pointed down the road to where her house was, which wasn’t too far from where he lived. It didn’t take a genius to figure out that Ella lived with her mom and her dad wasn’t in the picture. All he knew was that Ella and her mom moved in not to long ago.

 Mary was kind to her, holding her hand as they all crossed the street together to get to Ella’s house. The house was a little smaller than Dean’s, but not by much. The front door was painted beige, no windows on the door to look in the house. The mailbox was full, like it hadn’t been emptied in a few days. Ella took her book out of her bag, grabbing a pencil to begin her note. He offered to do it for her, making sure not to panic her mother.

  _Ella is safe at Mary’s house. House #26 just down the road._

 Ella had tape in her backpack, as if this was something that happened often. He didn’t want to pry too much into the little girl’s life of family. She taped the note to the door before putting everything back in her bag. He could see Ella was a little upset that her mom wasn’t there. Another indication that it was just her and her mom, much like it was just him and Mary. She quickly snapped out of it when Mary started telling her that they could play with her toys when they got back to her house.

 Mary had mentioned Ella a few times when he asked her how her day was. Ella was a nice girl who played with his daughter at recess. She ate lunch with her and had lots of fun with her, which is all he could ever ask for his little girl. Ella was Mary’s best friend.

 The second Dean unlocked the door, both of their shoes were off, running upstairs to Mary’s bedroom to play with her stuff. Giggling erupted right away, making him smile. He would have to be sure that he invited Ella over more often to play.

 He wasn’t sure how long Ella was staying, so he pulled out premade frozen pizza, knowing that was a safe bet for kids to eat. That way there was more than enough to eat. It also gave him enough time to go over the paperwork he needed to for his uncle before the workday tomorrow.

 Dean was a mechanic and had been since he was fifteen and his uncle taught him everything there was to a car. He loved his job, and it provided a steady income for him and his daughter for the time being. Given the chance, he would go back to school and study to be something different. He wasn’t giving up on his dream to be a firefighter, but he couldn’t do it when his daughter was only six and had no one to look after her when school was done.

 His uncle was going out of town for the week, leaving the shop for him to take care of. He left Dean in charge of going through the paperwork so he knew what he was getting himself into. That way if if he had any questions, he could ask him while he was still there. For the most part it was straight forward and he understood. Everything was adding up to what it was supposed to be.

 A knock on the door pulled him from his trance. It had to be Ella’s mother. He wasn’t expecting anyone else, and people didn’t stop in all that often without calling first, his uncle included. He put the pen down, rounding the counter to head to the door. He ran his hand through his hair and let out a sigh.

 He flicked the lock before twisting the knob on the door, opening it to see just who was standing at his front porch. A woman stood there, her eyes cast downwards just like her daughter’s was when he saw her earlier on in the day. When she looked up, he swore his heart was going to beat out of his chest.

 Now he understood why he recognized Ella. She was a spitting image of her mother. Y/N.

 The woman he had fallen for _ten_ years ago.

 The one he _let_ get away.

 “No way!” he breathed out.

 “Dean Winchester,” she smiled widely, pulling at his heart just enough for him to notice. She remembered him.

 “Y/N Y/L/N. How long has it been?” he questioned, trying to repress his smile from being to wide. God, she looked more beautiful than she did ten years ago. Her hair had grown out with that natural wave to it. She still did her make up the same way, soft and natural. Her smile still lit up a room.

 “Too long. Way too long,” she breathed out. “You look good, De.”

 “You look as beautiful as I remember, Y/N. I had no idea you were back in town.  God, I had no idea you had a daughter. Ella looks exactly like you,” he pointed out.

 “I had no idea you did either,” she let out a laugh.

 “You want to come in? I’ve got pizza in the oven. I wouldn’t mind catching up with you,” he suggested. She nodded her head, stepping inside his home. Dean wasn’t sure about a lot of things, but this? Having her here now? This had to be a sign of some sort. He swore the second she moved out of Lawrence with Nick, that he would never see her again. A lot had gone down between them back then. Now here she was, kicking her shoes off, ready to take a seat at the counter.

 He had dreamed of moments like this. He had dreamt of her for months and months after she left. She was his best friend a long, long time ago. She was the girl he’d go to for advice. The girl that was always there for him when he needed it. She was the one who held him together when his parents died. She was the only girl he has ever loved in his life, and he was damn sure she was the only one who he’d ever have those feelings for.

 But she was taken back then. She was with Nick from eighteen onwards. He swore that he’d missed his chance. That she and Nick would have been together forever. Nick didn’t deserve her, of course. He didn’t treat her nearly as good as she should have been treated. He wasn’t from the group of friends they had. He was an outsider at best, trying to weasel his way in and he did. They all thought she deserved better.

 But it wasn’t anyone’s decision to make but hers.

 “Thank you for taking care of her, Dean,” she said as she sat down at the counter, placing her hands on the countertop.

 “It’s no problem. You gotta do what you gotta do,” he shrugged.

 “I’m not usually late. I was late to work this morning, and my boss threatened to fire me so I had to stay an extra hour,” she breathed out, clearly not proud of herself.  Her eyes cast downwards, locked on her hands in front of her.

 “Hey, anytime you need me to watch her after school, let me know. I have no problem with it. Her and Mary are best friends by the look of it. She’s always welcome here. You’re always welcome here,” he assured her. A part of him praying that she’d take him up on that. He wanted her in his life. He wanted her the way he used to have her, even if it was friends. If he knew one thing, it was that he needed her to be a part of his life.

 “Thank you,” she said softly. “So where’s your no doubt, drop dead gorgeous wife that I have to be jealous of?” She was joking about the jealousy thing. She had to be. Y/N wasn’t the jealous type. Never had been.

 “No wife,” he chuckled. “No girlfriend either. Not many women want to date a guy with a daughter.”

 “You’re Dean Winchester! Have you looked in the mirror?” she let out a giggle. He had always known she found him attractive. She told him on a regular basis. But hearing her say it again, still made him smile nervously. She made him feel good about himself without even trying.

 “Oh yeah? What about you?” he played. “I don’t see a ring on your finger, which tells me you aren’t married or even engaged. So who’s the lucky guy?”

 “No one actually. Just me and El. That’s the way I want to keep it,” she revealed. An almost cold tone in her voice that hurt his heart. Someone had hurt her. Pretty bad at that. He prayed to god that it wasn’t Nick who hurt her. He’d kill him if he ever saw him again.

 “I feel you on that. My daughter is the most important person in my life. She’s my number one, you know?” he started. His mind thought back to his ex in an instant. He never wanted to put his little girl through something like that again. He never wanted her to see him upset like that ever again. He never wanted her to know about heartbreak, not this early. If he was going to die alone, then that’s fine by him.

 “Oh I know,” she agreed.

 “Can I get you something to drink?” he changed the subject. He didn’t want to have this conversation with her. He didn’t want to bring up everything he had been pushing down for three years. He didn’t want to open that back up again. Not now. Not ever.

 “Yeah, water would be great, thank you.”

 He turned around, grabbing a glass from the cupboard, pouring some water in it for her. He wanted to know what happened to her. He wanted to know why she was back. Why she wasn’t with Nick? If Nick was the father of her little girl.

 “Mommy!” Ella’s voice filled the room. Mary was following behind her. Her smile was wide as she saw her mom once more.

 “Hi baby!” Y/n beamed, hopping off the chair to pull her daughter in her arms. “How was your day?”

 “Good! No homework!” she stated.

 “Alright! You know what that means right?” she raised her eyebrow.

 “Movie night!” Ella cheered.

 “That’s right. But first, Mr Winchester here has invited us to have some pizza. You wanna stay a little longer?” she asked her. She nodded her head instantly. Mary jumping with excitement.

 “Pizza should be ready in ten, girls,” he informed everyone. His eyes locked with Y/N’s, taking note of how soft her smile was towards Ella. He had a million questions he wanted to ask her. But out of those million, he had zero ways to bring it up. She was Y/N, but she wasn’t the same Y/N. He didn’t know how to talk to her like he used to. He didn’t know what to say to her without crossing some invisible line.

 “So where do you work?” he asked her, trying to make some conversation.

 “The diner in town,” she informed him. “It’s all I could get when I moved here. Nowhere seems to be hiring. Not without some college degree that you need to work practically everywhere.”

 “You didn’t finish school?” his jaw dropped. “Y/N-”

 “No I didn’t. I got pregnant my last year and dropped out,” she shared. “Life didn’t exactly go as planned. But I don’t regret it for a second. Look… I don’t really want to talk about- talk about this.” Her voice wavered. His blood went cold. Someone hurt her.

 “I’m glad you’re back,” he changed the subject. “Missed you.”

 “I missed you too, Dean. I thought you woulda been outta here. How’s Sammy?”

 “He’s good. Pre-law at Stanford, the nerd that he is,” he chuckled. He grabbed the oven mitts from the top of the microwave, pulling the pizza out of the oven, placing it on the counter. Nice and crispy the way he and Mary liked it. He was almost thankful that it was done. Y/N was making him nervous. He could see she was trying so hard to make it seem like everything was okay with her, when things were clearly a little hectic.

 Dinner went by quickly, both her and Ella enjoying the pizza that Dean had made. He had invited both of them to stay for a little while longer, but she kindly declined. Saying something along the lines of unpacking and Ella needing a bath. He knew she was unsure of all of this, kind of like he was. He didn’t want to push her. He didn’t want to jump back into the same friendship they had like ten years hadn’t passed.

 He and Mary offered to walk them back to their house to make sure they got home safely. He also prayed that this walk would knock his daughter out so she’d go to bed on time. He figured spending a little more time with her friend couldn’t hurt.

 He told Y/N he’d see her again soon. She smiled sincerely before heading in her door. It was completely dark out now. All the streetlights were lit, lighting their short walk home. Mary took his hand, holding it tightly as they walked. Her bath would have to wait until morning. She was exhausted by the look on her face.

 He was carrying her in the door by the time they go home, taking her straight to her room. Toys were scattered all over the place from earlier activities. All that matter to him was that his little girl had a good day. The rest could be dealt with in the morning.

 She lazily changed into her pyjamas, dragging her feet as she headed to the bathroom to brush her teeth. Dean sat at the end of her bed, waiting for her to make her way back in the room so he could tuck her in and give her a goodnight kiss.

 “Daddy,” she yawned, crawling her way under the covers.

 “Yeah, baby?” he smiled softly at her.

 “Do you think one day Ella and I will be sisters?” she questioned. “That would be so cool.” Her question caught him so off guard that he was speechless. She was looking up at him with her gorgeous green eyes and freckle dusted nose; something she got from him. She had no idea how complicated that question was. To her, it was that she wanted to have Ella over all the time. To him, that would mean a life with Y/N. That would mean putting himself out there. That would be completely impossible for him.

 “I don’t know about that one, baby,” he whispered. “But it would be cool.”

 “Night daddy! I love you,” she smiled.

 “I love you too, Mary!” Sweet dreams!” He pressed a kiss to her forehead, making sure she was tucked in once more. He flicked off her light, shutting the door just enough before heading down the hall to his own room.

 He couldn’t put himself out there. No. There was no way. Y/N didn’t feel that way towards him back then. There was no way she would now. He couldn’t complicate things for himself and for his daughter. He couldn’t get involved with another person like that. Mary was his responsibility. She was his top priority. She came first, every time. He shouldn’t even be thinking about this.

 It was a pipe dream. Nothing that he could ever have. He didn’t want it.

 He couldn’t want it.


	2. Dean Winchester

**Summary for the Chapter:**

> Dean Winchester is a single parent to his six year old daughter, Mary. His daughter brings home her best friend, Ella, who’s mother is running late. He takes her in to wait, not quite able to place where he had seen this girl before. When she knocks on the door, he finally realizes just where he’s seen the little girl. She’s a spitting image of her mother, Y/N. The girl he fell for many years ago.

You were in the kitchen, preparing everything you needed for dinner. You were going to make parmesan chicken for the first time, with the recipe off of the food network. You weren’t the world’s greatest cook, but you could follow a recipe better than anything. You wanted to do something nice for you and Ella for dinner.

 You were grating the cheese when you heard the tiny footsteps coming down the stairs. Your beautiful little girl made her way over to you with a smile playing on her lips. Not just any smile. The smile that meant she wanted something and she desperately wanted you to say yes.

 “Hi kiddo,” you greeted her, looking at her with a smile.

 “Mommy,” she started, resting her arms on the table. Oh yes, she definitely wanted something. “Can I go over to Mary’s to see if she wants to play?”

 You thought about if for a second. You wanted her to be happy more than anything. You wanted to make sure that she enjoyed her childhood like you did growing up. But you also knew you were going to have to go with her. You were going to have to see Dean.

 “Yeah, okay,” you nodded. “Go get your jacket and we’ll head over.”

 You put all of your supplies away, covering up the chicken before putting it in the fridge. You could come back and work on it when you were done. Ella was quick in grabbing her coat, wasting virtually no time at all.

 You were out the front door within minutes, Ella’s hand in yours. The weather was on the cooler side for the beginning of September. Some sort of cold front making its way through the area.

 There was a part of you that prayed that Dean wasn’t going to be home and you’d have to go back home. But you knew it was a long shot with the impala in the driveway. Seeing him was hard for you. Especially with the history you had with him, and the way you left things between the two of you. It wasn’t right for you to be showing up on his doorstep randomly with a little girl. Even if your daughter was best friends with his.

 Ella ran up to the front door, ringing the doorbell before you were even at the end of the driveway. The door opened moments later, revealing Dean. He was standing in a blue, red and white flannel, a grey shirt beneath it and a pair of jeans that fit him perfectly. He hadn’t changed a bit.

 “Hi, Mr Winchester,” Ella greeted him. “Can Mary come and play for a little while?”

 “Of course Ella. You want to come in? Mary was actually just getting ready. We were going to see if you wanted to come over,” he told her. Ella nodded her head, stepping inside Dean’s home. “Hey Y/N.”

 “Dean,” you smiled softly.

 “You want to come in for a little? I can make us a cup of coffee?” he offered. You wanted to say no and your gut was telling you to walk away.  You wanted to go home and get what you needed to get done, done. But there was something in you that couldn’t say no to him. You never could say no to Dean.

 “Yeah, alright,” you nodded. He motioned for you to come inside with a smile playing on his lips. One cup of coffee couldn’t hurt, right?

 You kicked off your shoes and shrugged off your coat, placing it on the coat rack. Dean headed back into the kitchen, straight to the coffee maker to put on a fresh brew. You took a seat at the counter, placing your hands on the table. You felt a little awkward. You weren’t best friends like you used to be. You didn’t know what conversation to bring up, or even start. You didn’t know what to do other than twiddle your thumbs. Things were so much different now.  

 “So, what are you doing now?” you asked him.

 “I’m still working at the garage with Bobby. I co-own it with him now. It’s really good money and I get off just in time to get Mary off the bus,” he told you.

 “God, you’ve been there since you were fifteen,” you gasped, remembering the day he came over and told you that he got the job.

 “I love it there,” he shrugged. “There was no sense in going to school for something else when I was happy there.”

 “You wanted to be a firefighter if I’m not mistaken,” you pointed out, trying to supress your smile.

 “Yeah, I know. And honestly there is a part of me that still does. But I’m twenty eight. I’ve got a six year old daughter and it’s dangerous. I’m her only parent, and I can’t risk something going wrong and her having no one to take care of her.”

 “That’s fair. I’m glad you’re still happy at the garage,” you commented.

 Inside, you felt like you were a disappointment to him. You went to college and didn’t graduate. You were his best friend once upon a time. He always saw you as this perfect girl. You were so damn far from the girl you used to be, and you weren’t sure he was going to like the girl you were now. You dropped out of college, got pregnant, and now you were working a shitty minimum wage job that barely got you by. You didn’t want this life for yourself. This wasn’t the life you talked about with him ten years ago. You didn’t want him to see you the way you saw you.

 “So last time you were here, you told me you dropped out of college?” he brought up hesitantly. You froze instantly. “You ever think about going back or at least finishing up here?”

 “Every single day,” you admitted. “But Ella is number one.” Dean turned to face you, placing your cup of coffee in front of you. You could see it in the way he looked at you that he thought you were better than this. It was like he still had you on this high pedestal. It hurt a little to know that you weren’t gone to measure up to it.

 “One day,” he assured you. “Even if it means I watch Ella for you so you can get your degree.”

 “That’s sweet of you to say,” you swallowed hard. “But I hate to say that it’s not going to happen. I’m still trying to move in and make enough money to pay the bills.”

 “Your parents not helping you at all?”

 “My uh - my parents don’t talk to me anymore,” you paused. “Sorry, that’s a lie. They call and say ‘Ella’ and that’s the only communication we have. To them, I’m a disappointment. They talk to Ella for the sake of talking to their granddaughter, but me? I’m the one who didn’t finish college, and marry Nick. I didn’t do anything they expected of me.”

 “God, I’ve always hated your parents,” he revealed, shaking his head. “Y/N, you are doing perfectly fine as a single mother. You’re Y/N and you can do anything you put your mind to. You always have been that way. It’s one of the things I admire about you.” His words made you tear up. You didn’t expect them to mean as much to you as they did.

 Dean grabbed the milk out of the fridge, placing it on the counter for you to add it to your coffee. You couldn’t help but admire how nice his house was. It felt like a home compared to yours. Then again, he had a job to pay for it. You were going to consider yourself lucky if you could pay the bills this month.

 “You want to stay for dinner?” Dean offered, taking a sip of his coffee.

 “Uh, no thank you. I’ve got something already in the works tonight,” you shook your head.

 You couldn’t stay for dinner. Not just because you were making parmesan chicken. You couldn’t stand to be in Dean’s house after the way you left things ten years ago. Dean wasn’t your best friend anymore, and he wasn’t going to want to jump back into a friendship that clearly wasn’t what either of you thought it was. You betrayed him. You hurt him. He wasn’t going admire you the same, not once he got to know you. He was going to see you when you dropped Ella off to play with Mary. A few kind words were going to be exchanged and you’d be on your way. And you deserved it. The guilt was eating away at you for sitting in his home. You couldn’t stick around and pretend everything between the two of you was copacetic.

 Casual conversation was exchanged, and you tried your hardest to fake a smile, and get through it. You drank your coffee and when that was done, you knew you had to get going. There was a lot of stuff you wanted to get done before the work week started again.

 “Before you go, I’m going to give you my number. You know, in case you work late. That way I can take care of your daughter until you can get her,” he offered. You shook your head once more. “What?”

 “I don’t want to have to rely on you,” you whispered.

 “You’re not, but I get it. You can run late from time to time. It happens,” he said sincerely.

 “Yeah, but-”

 “No buts. I just want to help you out, Y/N. I just want to make sure you have someone you can count on. I get what it’s like. Being a single parent and all.”

 “Alright,” you sighed in defeat.

 On your walk back to your house, you couldn’t help but think about how Dean wasn’t going to stick around forever. He was soon going to be reminded of everything that went down between the two of you. You couldn’t rely on him when you could barely rely on yourself. You didn’t want your daughter to grow older and resent you.

 That was your greatest fear. Just knowing that someday she was going to resent you for not having enough money. Kind of like you resented your parents growing up because they tried to control every aspect of your life. But this was different. You were never going to be able to put enough food on the table or give her the things she really wanted. You were trying so damn hard but it was never going to be good enough. You were her mother, and her father in one. And someday she was going to ask about her father.

 Dean told you he was going to bring your daughter home in a couple of hours. He offered to come over with you and help you out but you politely declined. You didn’t want pity, and you didn’t want him to feel like he had to feel sorry for you because you were barely scraping by. You at least wanted to get the rest of Ella’s room unpack so that if Mary was to come over, they could comfortably play in her room.

 Ella wanted to paint her walls pink and green. She had picked out the colours a few weeks back when you had gone out to Walmart together. You were saving your tips in order to be able to afford it for her.

 You got to work in the kitchen. You needed to finish up preparing the chicken before you moved on to something else. You needed to eat dinner. You had to make sure that everything you wanted to get done today was done in order to feel like you accomplished something.

 It didn’t take long to get the chicken ready with what you already had prepared before stopping off at Dean’s. You placed it in the oven and headed up to her bedroom.

 One of the things she really wanted to have was her bookshelf. She wanted to be able to put her books on the top shelf, and her toys on the bottom. You wanted her to feel at home when she was in her room.

 You opened up the door and smiled to yourself. She had tried to make her bed the best she could. She had put up a few new drawings since last night when you putting her to bed. One was of you and her driving in what looked to be the last town you lived in. It made you wonder if maybe she missed it there. Then there was one next to it of her and Mary. The only real friend she’s had in her life. Her friendship with Mary reminded you a lot of what things were like for you and Dean growing up. You were like two peas in a pod for a long time.

 You spent a lot of time putting her bookshelf together. You made sure it was safe before putting her books up on it. Her room had a good vibe to it. It felt warm and inviting compared to the rest of the house. That’s the way you wanted it for now. You wanted it to be warm for her sake.

 By the time you finished, you heard voices coming from downstairs and you knew one of them was your daughter’s. Time had flown by since you dropped her off. You walked down the stairs, only to find Ella standing by the front door with Dean and Mary with her. Dean’s eyes met yours for a moment. You turned away in seconds, almost ashamed of how your place looked.  

 “I’m home, mommy!”

 “I see that, baby girl,” you grinned widely.

 “Did you finish my shelf?” she questioned with a wide smile.

 “Yes I did. You can go take a look,” you winked.

 “Hey Y/N, can I talk to you for a sec?” Dean asked. You nodded your head. Ella and Mary kicked off their shoes, heading upstairs to go see her room. You stood sheepishly in front of Dean. You were not ready for whatever he was going to say to you.

 You motioned for him to follow you into the kitchen, praying that he’d ignore the stack of boxes next to the back door. Dean stood tall compared to you. Confident compared to you. You swallowed hard, looking up at him with a hesitant smile.

 “Are you okay?” he asked you. His expression completely serious, and even a little bit concerned. You had no idea how to even answer his question.

 “Yeah, of course?” you furrowed your brows, hoping that he’d believe you.

 “I mean it Y/N. Are you okay?” he started. “I know that it’s been awhile since we’ve seen each other. But to me, you seem like you’re not okay. You barely want to stick around when I ask if you want to stay. You have trouble meeting my eye sometimes.”

 “Dean, I’m a single mom, and I just moved here not that long ago. I’ve barely had time to unpack,” you told him, trying to stay as calm as possible.

 “I can help, you know.” he offered you.

 “It’s okay, Dean.”

 “Y/N, c’mon! There’s more to it than that-”

 “You’re right,” you breathed out, trying to keep yourself from losing it on him. Especially when he didn’t deserve it. “But I have another person’s life to take care of before mine. I have a job I need in order to feed her and take care of her. I come second, you should know that.”

 “Are you okay financially?” he questioned. “I know that’s personal-”

 “I’m trying, okay? I’m trying my hardest.”

 “If you need help-”

 “I’m not going to ask for help. Especially not from you, Dean.”

 “Why not?”

 “You see me as this perfect girl you once knew. I don’t want you to see me the way I see myself, Dean. I don’t want you to see any of that.” God, those words just came out of your mouth and Dean heard them.

 “You’re a single mom, Y/N, You have all the responsibility, just like I do for my little girl. It’s a lot to do. And I know we are two different people now, but it doesn’t mean that I don’t want to be a part of your life. I’m here if you need anything. Anything at all, okay?” he told you.

 “Thanks De.”

 “And for the record, there is nothing that you could say, or do that would make me see you as anything less than the girl I know. Perfect or not, you are still Y/N. You are still the girl that I grew up with.”

 “But like you said, Dean; we’re two different people now,” you raised your eyebrow, trying to make a point. And you couldn’t forgive yourself for the way things ended between the two of you, you thought to yourself.

 


	3. Superman

**Summary for the Chapter:**

> Dean Winchester is a single parent to his six year old daughter, Mary. His daughter brings home her best friend, Ella, who’s mother is running late. He takes her in to wait, not quite able to place where he had seen this girl before. When she knocks on the door, he finally realizes just where he’s seen the little girl. She’s a spitting image of her mother, Y/N. The girl he fell for many years ago.

**Notes for the Chapter:**

> WARNINGS: Mentions of Sexual Harassment, Self Doubt, Bit of Angst, Fluff.

Dean was at work, fixing up a car when his phone went off. It was a text from her, asking him if he can take care of Ella for a little while. She needs to work late. He smiled to himself instantly understanding her situation. He was more than proud of her for texting him that she needed help. He was quick in responding to her, telling her he’d be happy to, and he is. He loves that his daughter has a best friend, and it just so happened to be his high school best friend’s daughter. It just meant that he’d have the chance to see her when she picked up Ella later.

 She had been pretty distant for the past couple of weeks. Hell, since he first seen her really. Some days were better than others. It all depended on what day of the week it was. She was struggling and he knew she was. Anyone with eyes could see that she was trying her best to not give up. But she was also Y/N, and she didn’t accept help from anyone. She was stubborn like that. He had a good indication that she didn’t have a whole lot of money and that was why she had to work later some days.

  He was pretty set. He didn’t have a college education to pay off, and he has had a savings account since he was fourteen. She was different. Her parents were rich, and made that pretty known. Her parents were also some of the shittiest people in the world. If he knew them, he knew that there was no way they were going to help her out. There was a part of him that wanted to help her out. After all, she was his best friend ten years ago and she barely had her head above the water.

 It was more than that though. She was distant for a whole other reason. She kept him away from her, and a good amount at that. She wasn’t the same girl that would have been all over him like she was as a kid. Constantly hugging and touching him. She was affectionate growing up. She loved hugs and kisses on the cheek. Hell, she was always kissing his cheek or his forehead, especially after his parents died. It was her way of comforting and being comforted. Now, she was quiet, and reserved. She didn’t speak a whole lot, not unless someone said something to her first. Not to mention, there was the comment she made about him thinking she was perfect, and her not wanting to change that. Dean knew then, she had been through something that changed her. Something that she didn’t want him to know about. Something she didn’t want anyone to know about. She was trying to remain strong for her little girl. But there was no one there to catch her when she broke.

 He could never see her as anything other than the girl he loved. The girl that held him when he needed it. The one that was there for him. The girl that got away. And even if she had changed, it didn’t mean that he wasn’t going to fall for the girl she grew up to be. His feelings for her haven’t changed. They just remained dormant. They had always been there. He’d be damned if he was to let her get away this time without a fight.

 He waited for Ella and Mary to get off the bus. It had warmed up significantly after the cold front, and he had dressed Mary in a t-shirt and shorts to school. He hated early September. The weather was up and down. Not to mention the wasps were the worst this time of year. Every time he was nervous he was going to get a call from the school to say she had been stung and had an allergic reaction.

 The bus pulled up to the corner, letting out four kids, including Ella and Mary. Both of them were laughing at something. Ella was dressed similar to Mary, only her hair was done up in a high ponytail. She looked a lot like Y/N did when she was a kid.

 “Hey girls,” he beamed, watching both of them walk over to him. “Ella, your mom’s working late today so you’ll be hanging out with us until she finishes. Is that okay?”

 “Yeah, I like your house,” she nodded. Dean didn’t have to worry about her saying no. Just like last time. What he didn’t expect this time was for Ella to reach up and take his hand. Sure they were crossing the street, but usually her and Mary held hands. This time, he was in the middle of the two of them. It made him incredibly happy. Happy that Y/N’s daughter trusted him.

 Both the girls held his hand the entire way back to the house. He could tell they were happy it was Friday. A long week at school would do that to them. He expected them to run straight upstairs to head up to Mary’s room to play with her toys. Instead, they took a seat at the table, pulling out their homework to work on it. The dad in him was so proud. Even if it was a Friday night and she had a few days to get it done. At least they could enjoy the weekend it it was done.

 “You girls want fries and nuggets for dinner?” he asked both of them. Ella shook her head no, and that confused him a little. “Why’s that?”

 “I don’t want to eat dinner without Mommy,” she shook her head. That made him smile and frown all at the same time. He could hear in her voice just how much Ella loved her mom. After all, it was only the two of them. It’s all she knew.  

 “We can wait for your Mommy to come home,” he assured her. “What’s her favourite food?”

 “She likes burgers,” Ella stated. “Burgers and french fries.”

 “Well, we can have that for dinner instead,” he shrugged.

 “Yes please, Mr Winchester,” Ella grinned.

 “Your mom still likes burgers, huh?”  Dean smiled, remembering that she loved a good burger when they went out together.

 “Oh yes. It’s weird,” Ella giggled.

 “Mary, you okay with fries and burgers?” He asked his little girl.

 “Of course, Daddy!” She beamed. “Your burgers are the best!”

 The girls finished their homework and went up to Mary’s room right after. He pulled things out of the freezer, trying to prepare something to eat for dinner. He was going to take this chance to spend a little time with Y/N. To get to know her again. To become friends again. He wanted to be a part of her life again.

 He was brought out of his thoughts by soft knocking at the door. He knew she was on the other side and he was excited to see her. He had been since she texted him earlier on in the day. He headed over to the door, straightening out his shirt before he opened the door. Y/N was standing on the porch with one arm crossed over her body and her head cast down. She took a deep breath before looking up, her eyes puffy and a little red. She was upset.

 “Hey, what’s wrong?” he questioned urging her to come inside. This time she didn’t protest like he thought she would. He wanted to throw his arms around her, and comfort her in the only way he knew how. But he wasn’t sure if she was okay with something like that. He didn’t want to push her away. He didn’t want her to hate him.

 “Rough day,” she smiled weakly. He could see the tears welling in her eyes once more. “I’ll get out of your hair in a second.”

 “Stay,” he asked her. “I’m making french fries and burgers, per requested by Ella.”

 “Dean-” she protested.

 “C’mon. You’ve had a rough day, it’s Friday night, I’m making dinner. You’re daughter is with mine. Might be better for you to unwind here before going back to being a responsible adult,” he suggested.

 “Can I go home and change?” she whispered.

 “Absolutely. Go home and put something comfy on, okay?”

 “De?”

 “Yeah, sweetheart?”

 “Thank you,” she muttered, a single tear slipping down her cheek. He knew right then she needed someone. She needed a friend. She need someone to be there for her. He could be that guy once more.

 She was back quicker than he expected. She still had that sad glimmer in her eyes and they were a little redder than before. He knew she went home and cried.  She must have had a really tough day. He wanted to punch whoever made her feel like crap.  He gave her a warm smile. She tried to reciprocate as she stepped inside. She headed straight to the counter, taking a seat where she sat the last time she was here.

 “Can I get you something to drink, Y/N?” he offered her.

 “Can I just have a glass of water?” she requested. He nodded, opening up the cupboard to grab a glass before pouring some out of the dispenser in the fridge.

 “Dinner will be ready in a few. I’ve got the burgers in the oven since I don’t exactly have a working barbeque right now,” he told her.

  “Thank you for having me over,” she said to him. Her eyes actually met his and stayed there for a few seconds longer than usual.

 “You’re welcome here anytime,” he assured her. “Ella has already done her homework, just so you know. They both came in and sat down to do it before they headed upstairs.”

 “Ella likes to do it right when she gets home so she doesn’t have to worry about it later,” she shared.

 “Just so you know, I’m here to talk if you want to talk about your day,” he offered.

 “I know,” she nodded. “If you’re not busy. Maybe I could stay a little while?”

 “Absolutely. The kids will be happy to have more time to play. Maybe Mary will actually go to bed on time for once. Besides, I wouldn’t mind spending some time with you. Movie, popcorn and sharing a small blanket sound good to you?”

 “Just like old times,” she chuckled. “Nine times out of ten, I fell asleep on your shoulder.”

 “Hey it that’s what you need,” he laughed along with her. “You’re welcome to stay as long as you want to.”

 “Thanks De.”

 The kids came down for dinner, both of them giggling, just like they were when they got off the bus. It was nice to see his little girl happy. She had a best friend. Someone to be there and spend time with. Someone that she could grow up with and that’s all he ever wanted for his little girl. He wants her to feel that love. He wanted her to have a friendship like he had growing up. Hell, he wanted that friendship back for himself, the more he thought about it.

 “Mommy, how was work?” Ella asked her mom.

 “It was okay,” she answered. “Burnt my finger on some hot coffee today.”

 “Do you need me to kiss it better?”

 “I’d love that,” Y/N grinned. Dean watched as Ella walked up to her, taking her hand to kiss it.

 “All better, Mommy.”

 “How was your day today, Ella?”

 “It was so good! Mary and I were playing on the monkey bars at recess and Mary made it the whole way around without falling,” she went on. “We’re also reading the same book.”

 “That’s so cool,” she told her. “Mary, you must have some good upper body strength to make your whole way around. I couldn’t even do that as a kid.”

 “Daddy says I’m strong,” Mary grinned.

  “You are, kiddo,” Dean winked.

 “So strong,” Y/N added.

 Dean noticed the way Ella looked at her mom. It was exactly like the way Mary looked at him. Like they were looking at their entire world. He couldn’t help but notice that Ella’s eyes were blue, a different, yet familiar blue. Not the same colour as Y/N’s eyes. It made him wonder once more if Nick was Ella’s biological father.

 Dinner went off better than he expected. Everyone seemed to enjoy the burgers that he made. Ella even told him that they were the best burgers she had ever tasted. That made him smile. Y/N even complimented him on how good they were. He knew he did something right.

  The girls took off, leaving them to do the dishes. He threw everything in the dishwasher and motioned for her to head over to the couch. He took off to grab a blanket for her, just like old times.

 She sat in the corner of the couch, bringing her knees up to her chest before resting her chin on them. He walked over to her with the blanket, handing it to her with a smile.

 “I was almost fired today,” she confessed. “That’s why I had to stay late. It was either that or I was gone and I really need this job.”

 Dean looked at her, taking in her words. He hated her boss, that was for sure. But he couldn’t help but smile on the inside. She told him what she was upset about. That was a start. It was more than he could ask for.

 “You deserve better,” he simply told her as he took a seat next to her.

 “I can’t exactly get better right now,” she mouthed. It was clear she was trying not to cry once more, but she was failing. “He’s been telling me to drop a button on my shirt for the last two weeks. And because I’m uncomfortable, he likes to tell me that I’m not good enough. I can’t quit because I need the money to survive.”

 “That’s still not okay. It’s harassment. It’s making you uncomfortable,” he reminded her.

 She went quiet again and that concerned him. He wanted her to feel comfortable around him like she used to be. He wanted her to be able to tell him what was on her mind so that it wasn’t bottled up and buried until she exploded.

 “C’mere, Y/N,” he muttered, opening up his arms for her to crawl into. She found comfort in hugs, he reminded himself. He wanted to provide her with that same comfort he used to offer. He was surprised when she shifted, throwing her arms around his waist to cling onto him. He instantly loved the feeling of having her in his arms again. She always fit so perfectly. She melted into him, accepting his embrace. He just wants to hold her. He wanted to take away the sadness and the anger and replace it with warmth.

 “Thanks for this Dean.”

 “It’s no problem,” he mumbled.

 She pulled back, releasing him. He frowned immediately  when he saw the tears welling in her eyes. He never wanted to see her cry. He didn’t want to see her upset. But she was.

 “No seriously. Thank you! It’s been a really long time since anyone has been here for me. Even longer since that person was you and god, I missed you so much, Dean.” He couldn’t help but pull her into his arms once more. There she was. The girl he knew. The girl he fell in love with all those years ago.

 “I missed you too, trust me,” he admitted.

 “De, about the night I left-”

 “Y/N-”

 “I didn’t want to go,” she breathed out. “He forced me to come with him. My parents told me I was going with him. That I was going to the best school for my program. But I knew he was the reason why they wanted me to go. Nick was this nice guy to them. They paid the second I got accepted. I knew what he was like.  It was almost like he - he wanted me away from everything I loved and away from you. I couldn’t talk to Charlie or Cas. Benny. I wasn’t allowed to talk to anyone. It was part of a fresh start. He knew we were close, Dean and he didn’t like that. He didn’t like what he couldn’t have control of.”

 “He was a dick,” he muttered.

 “I know. And I wish I would have listened to you.”

 “Y/N-”

 “You were right Dean, and you know it.”

 “I have to ask. Is Ella-”

 “Yes. She was his”

 “Was?”

 “He left the second I found out I was pregnant. He bailed and there was a part of me that couldn’t be happier that he did. It’s not like our relationship was good. He was hot and cold, we were on and off. He cheated more times than I can count. Then I got pregnant and he was nowhere to be found. My parents disowned me. I’ve been on my own since I was twenty two.”

 “Then why did you come back here now? You’re twenty eight.” he questioned her.

 “Because Ella was going to have no life where we were. I could see she was struggling, and she wasn’t happy. She didn’t have a whole lot of friends. Our apartment had one bedroom and it was hers. I had no other option than to come here. At least I knew all about this town. She could grow up here. I couldn’t keep her in the apartment and sleep on a couch for the rest of my life.”

 “I’ve got your back, Y/N. Whatever you need. You’re not going to end up like that again. I promise.”

 “What about you, Winchester?”

 “What about me?” he chuckled.

 “How come you have no woman in your life? You’re a catch. You’ve only got better with age,” she brought up. “Mary’s mother?”

  He froze instantly.  He didn’t want to tell her. He couldn’t. He couldn’t go back into those memories. He didn’t want to. It would only hurt him. And he didn’t want her to see that he’d been hurt. That he was damaged goods now. She had stuff she was dealing with and she certainly didn’t need to worry more about anything.  

 “She’s not in the picture anymore,” he revealed. “Haven’t really considered moving on either. Mary’s number one.”

 “I get that.” she agreed. “Being a single parent kinda sucks though. It’s hard to be a Mom and Dad”

 “Being a Mom and a Dad is hard. Although, if you’re sticking around, I might have to get you to have the period talk with Mary. You’d be better than I would,” he joked.

 “I don’t even want to think about that,” she let out a laugh. “She’s only six.”

 Mary came running down with Ella, both of them with matching smiles, which only meant one thing. They wanted something. Mary sat on Dean’s lap, her hand coming up to his cheek, something she also did when she wanted something. He knew that one well enough. He gave in every time.

 “Daddy, can Ella have a sleepover tonight?” she pleaded, using those puppy dog eyes her uncle taught her. Damn Sammy.

 “We just gotta check if it’s okay with Ella’s mommy,” he smirked. “Y/N?”

 “Yeah, you can have a sleepover. I’ll go home and pack your bag in a little bit.” Y/N agreed. A part of Dean wanted to ask her to stay the night too. He knew it’d be too much thought. But he wanted some time to hang out with her and talk to her like he used to. He missed his friend and he wanted to get to know her again. He wanted to hold her a little while longer and watch movies with her life old times.

 “We can come with you when you’re ready?” Dean suggested. “That way you’re not walking out all by yourself.”

 “Sounds good. We’ll go in a little while. I’m just going to hang out with Mary’s Daddy for a little while longer. Catch up with him.”

 “Okay, Mommy! Thank you!” Ella beamed.

  “I uh- I was wondering if maybe you wanted to stay too? That way you’re there if she needs you. We could hang out, like old time, and get to know each other again,” he asked nervously. He knew his chances were slim, but he’d forever kick himself if he didn’t.

 “I’m sorry, Dean. But I’m just not ready for that yet,” she admitted.

 “That’s okay,” he reassured her. “I get it and I can respect that.”

 “Thank you,” she smiled at him.

 “Want to watch a movie before you have to go?” he questioned.

 “Of course I do,” she nodded.

 He ended up putting in Jumanji, a classic they both liked. He wanted to spend more time with her. He wanted to ask her out. And there was a part of him that wanted to be with her the way he was with his first ex, Cassie. He had always had feelings for Y/N. He had always wanted her, and maybe her showing up was his chance to have her. To make her life easier and love her the way she deserved to be loved. Nick took advantage of her from the start. She probably had this screwed up ideation of what a relationship was supposed to be. If anyone was worth moving on to, it’d be her.

 He knew she was the one for him. He just hoped someday she’d feel the same about him.

**Notes for the Chapter:**

> Feedback is greatly appreciated!


	4. Blast From the Past

**Summary for the Chapter:**

> Warnings: Fluff, Cigarette Smoking, Underage Drinking, Vomiting, Mentions of Death, Self- Loathing. 
> 
> Summary: Dean Winchester is a single parent to his six year old daughter, Mary. His daughter brings home her best friend, Ella, who’s mother is running late. He takes her in to wait, not quite able to place where he had seen this girl before. When she knocks on the door, he finally realizes just where he’s seen the little girl. She’s a spitting image of her mother, Y/N. The girl he fell for many years ago.

Dean and the girls walked you back to your house so you could grab Ella’s stuff. Ella wanted to help you get her stuff for her. You knew Dean was going to look around while he was waiting for the two of you to come back. Ella came down with her bag ready to head over with the Winchester’s. You could see it on her face that she was excited. You remember that feeling all too well when you got to have a sleepover at a friends house. 

 You walked her to the front door where Dean and Mary were waiting. You crossed your arms over your body as she put her shoes back on. It was definitely going to be a little strange without her for the night. 

  “Bye Mommy! Love you!” she smiled, blowing you a kiss before she headed out the front door with Mary. 

 “What are your plans for tomorrow?” Dean asked you. A soft smile playing across his pink plump lips. 

 “Grocery shopping. Yay!” you chuckled. “What about you?”

 “How about you come over tomorrow night and I’ll cook you a really nice dinner. Ella can hang out with Mary, I’ll get to spend time with you,” he offered. He pulled his bottom lip between his teeth, hoping your answer would be yes. After how well the night went, you wanted to. Spending time with Dean wasn’t as scary, not after he hugged you close to him earlier on. Ella would enjoy spending time with her best friend.

 “Dean Winchester, are you asking me on a date?” you joked, trying that teasing tone you once had with one another. 

 “Half -date actually,” he said nervously. His hand coming up to the back of his head, scratching at the small hairs. His nervous tell. 

 “Half date?” You furrowed your brows. 

 “Yeah, I mean, I can’t exactly ask you to go out, since we have no one to watch the kids, but I want it to be a bit more date like,” he revealed. You swore your heart leaped in your chest, and cracked at the very same time. You weren’t good enough for someone like Dean. Most of all, you weren’t good enough for his daughter. You were barely holding it together for your own. But you couldn’t say no to him. You didn’t want to disappoint him once more. 

 “De-”

 “It doesn’t have to be-” 

 “Yes. I would love to have a half date dinner with you.”  you agreed happily.

 “Really?”

 “Yeah. Why do you sound so surprised, Dean?”

 “Because I never thought you’d say yes to a date with me,” he chuckled sheepishly. It had to be the _best friends_ thing in high school. Things were different now. You were both _different_ now.

 “Well, my answer is yes,” you grinned. “Take care of my baby, would you? Make sure nothing -”

 “I know, sweetheart. Single parent too, remember.” he chuckled. “I’ll always protect her like my own.” 

 “I know. I just worry. I trust you to take care of her. Please call me if anything goes wrong. She’s not allergic to anything. Don’t give her too much chocolate milk or she’ll throw up, and she’s scared of thunderstorms. Not that we’re getting any rain tonight..”

 “Y/N, it’s fine. Don’t worry,” he reminded you, reaching his hand up to your bicep, giving you a reassuring squeeze. “I won’t let anything happen to your girl.”

 “Thank you, De.”

 “I’ll see you tomorrow,” he winked, taking off through the front door. 

 Dean took off down the street with Ella and Mary’s hand in each of his. You couldn’t help but watch them go. The skip in her step. She was happy and that’s what mattered the most. You trusted Dean with your daughter. He’d never let anything happen to her even if it killed him. 

There was a part of you that wanted to stay the night with Dean, but it wasn’t something you were up for. Not with Dean. You weren’t sure you could let yourself fall completely for Dean. Not after years and years of history.  Clearly he liked you, he asked you on a half date and that wasn’t something too out of your comfort zone. You could bring your girl and she’d have his daughter. But you weren’t ready to go there with Dean. Not after what you did to him. Sure he said it was okay and all, but it wasn’t. Nothing about what you did was _okay_. You left all your friends behind for a guy that didn’t even love you. You couldn’t be selfish, not now that Ella was your priority. You weren’t about to give her the wrong idea that you and Dean were ever going to be something more.

He didn’t want more either. It was nothing more that two single parents getting together so their kids could hang out. Every kid’s dream. Your dream twelve years ago. 

                  ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

  _You heard knocks at your window, startling you. You kicked your covers off and opened the window, only to find Dean on the tree branch outside. It was a little after eleven on a Friday night. You were confused as hell, but very happy to see him._

_“What are you doing here?” you whisper yelled, not wanting to attract the attention of your parents._

_“Getting you. C’mon. Get dressed, we’re going out,” he urged you._

_“Where?”_

_“Somewhere fun! Hurry. I don’t want your parents to catch me.”_

_You got dressed quicker than you ever had, grabbing your bag before slipping out the window with Dean. He was down the tree first, opening his arms out for you to jump from the tree into them to help you down. You could never get down on your own. Only up. You ran down the street with his hand in yours to where is impala was parked, taking off down the street. You told him he was crazy, but you loved the feeling of being in his car this late. Even more so when you snuck out. You didn’t care where you were going. As long as it was with him._

_He took you to a party at the farm by the lake that someone from school owned. Some rich kid who’s parents were never home. Everyone in your grade was there, including all your friends. Charlie, Hannah, Benny, Cas and Josee. The group of you were a tight nit pack. Not popular but not losers either. Dean played baseball with the guys, you girls cheered them on louder than the cheerleaders._

_There was a big bonfire by the lake. People were roasting marshmallows and drinking. Some smoking their weed and cigarettes. You guys stuck to one area. Dean walked with his arm wrapped around you. You loved nights like this. These were the nights you were going to remember when you looked back on your high school days._

_You all chatted and enjoyed each other’s company, enjoying a few drinks and sharing a cigarette with everyone. You could see that Henry and Josee were getting more and more flirty everytime they were together. He was one of the popular guys, but he always made his way over to talk to her every chance he got. Eventually, they excused themselves to go off in private. Cas and Hannah doing the same not long after. Benny had met up with the girl you knew he was talking to, Andrea you think her name was. Charlie snuck off to talk to a girl she liked in her drama class. That left you and Dean. You took off  and sat in the gazebo, lit with some old christmas lights. You could still see the fire and the commotion going, hear it even. You took a seat on the thick railing, Dean sitting on the other side._

_“Everyone’s all paired up huh?” he brought up._

_“Except you and I. How are you still single? You’re fucking gorgeous, Dean,” you questioned, your eyes meeting his._

_“Probably because I spend all my time with you,” he chuckled, sending you a wink.  “People think you’re my girlfriend.”_

_“We’re close, what can I say? I wouldn’t change that for anything,” you giggled. “I’m actually pretty drunk right now. Don’t know how the hell I’m going to get back in my bedroom like this.”_

_“Bobby’s away for the weekend, if you want to crash at my place. At least until you sober up,” he suggested. “There’s no way we’re getting you in your bedroom window quietly.”_

_“How are we going to get there?”_

_“I had one drink when we got here two hours ago. I only had half of it before Charlie stole the rest. I’m fine to drive.”_

_“Hey Dean,” you breathed out, Dean moved closer to you in an instant, standing next to you. His eyes never left yours as he waited for you to continue. “You ever wonder if all of us are still going to be friends ten years from now? Think we’ll all have our degrees and have get togethers once in a while?”_

_“Maybe,” he shrugged. “But if I’m being honest, the only friendship that matters the most to me is ours. We’ve been friends since we were six, Y/N. The rest of them came after us. ‘Sides, you’re the one who knows all my secrets,” he teased, making you smile. “I’d be happy to have get togethers with everyone, but if you and I don’t live at least down the street from one another then that’s a  big problem.”_

_“I can agree to that,” you giggled. “Here’s hoping in ten years time, you’ll be a firefighter or a doctor. I’ll be a teacher or a nurse, and everything will have worked out for us.”_

_“Certainly not too much to ask for,” he shrugged. “Ten years away. We’ll be twenty six. A lot can happen in ten years. I don’t doubt for a second that in ten years, you’ll be successful and happy._ _”_

_You and Dean stayed in a comfortable silence for awhile. At some point you got cold, and Dean wrapped his arms around you to try and kept you warm. You felt safe, and warm. Listening to the night sky as the rest of the party went on._

_You felt close to him, like somehow, maybe Dean was the one you were meant to be with in the end. He was the one out of everyone that was your soulmate. You relaxed into him with that thought, and just like that, he held you tighter. Dean saw you when he looked at you. He knew you. If you were married to him in ten years, you’d call yourself happy and successful._

_After some time, Dean suggested that the two of you head home. It was after two in the morning, and most of the party was dying out. He helped you off the railing, wrapping you in close to him. You had your arm around his waist, using it to keep your balance. The alcohol in your system was making you feel off._

_As soon as you got back to Dean’s place, you made a beeline for the bathroom, emptying the contents of your stomach. Dean was behind you, holding your hair back, making sure you didn’t get any in your hair. You felt horrible. Horrible for throwing up, and worse because Dean had to hold your hair back._

_After some time, you leaned against the wall. Dean took a seat next to you. You instantly rested your head on his shoulder, finding comfort. You told him you’re never drinking alcohol again. Of course, he laughed._

_“My parents are going to kill me when they don’t find me in my room in the morning,” you stated._

_“Since when do they come in to wake you up?” he asked._

_“Since Mr Colt called to tell them that I handed in that assignment one day late,” you told him. “I don’t know how much longer I can keep trying to meet their unreasonable expectations. I don’t even want to try anymore, Dean. I’m going to fall short anyways. I always do.”_

_“You’re doing amazing. It was one assignment, not the whole damn class. You always said Colt had it out for you. It’s not going to stop you from getting into college. Trust me.”_

_“How are you doing, De? It’s been six months since-”_

_“I know,” he nodded, speaking quietly. “It’s been hard, you know that. I worry more about Sammy. He’s only twelve and lost both of his parents. I’m trying for him. He needs me to be strong for him and I try to be. I really do. I hear him crying some nights, and I know there’s nothing I can do to make him feel better. I can’t bring them back. It’s just me, and Uncle Bobby and Aunt Jody. And they are great. They really are, but it’s not mom and dad. He’s not going to have the guidance that he needs when he gets older, and I worry I’m not going to be enough sometimes. But all I can do is try, right?”_

_“You didn’t answer my question, Dean,” you sighed. “How are you doing?”_

_“Y/N.”_

_“I know you don’t like to talk about things that have hurt you, or are hurting you. But you gotta know I’m here for you. I’m here to help-”_

_“And you have been! Trust me. Why do you think I’ve spent all my time with you? I can’t ever thank you for being there that night,” he sniffled. “I’d be dead without you, you know that?”_

_“I kind of love you Winchester. I need my best friend. I take care of the ones I love. You’re my family,” you reminded him. “My head hurts.”_

_“That’s because you’re short and drank too much,” he chuckled._

_“Never drinking that much again,” you groaned._

_“You’ll be saying that again when you wake up tomorrow. Let’s get you to bed,” he told you. He stood up first and bent down. He lifted you into his strong arms, carrying you out of the bathroom, and down the hall to his bedroom. You were so thankful he had a queen sized bed, not like the twin one you had at home. He carefully placed you down on the bed, flicking on the lamp._

_“Sweetheart, I’ve gotta change your shirt. You’ve got a little bit of vomit on you,” he told you. His voice was kind, and there wasn’t a hint of disgust. You sat up, raising your arms for him to take it off. He was back in an instant with a new shirt for you, not even taking a chance to look at you. Most guys would have but not Dean. You helped him move you into his bed, crawling under the covers. He joined you afterwards, keeping a safe distance between the two of you. Sleepovers never involved cuddling, even if you wanted to._

————

 You climbed into your bed after locking all your doors. Your mind reeling over Dean and the thought of that night. The night you were almost convinced that you and Dean were meant to be. But it also made you realize how much you must have hurt him by leaving. By walking away from him. You didn’t deserve a second chance. You didn’t deserve to be a part of his life. You chose and you chose wrong. You gave into the first guy to give you attention and look where you ended up. 

 Dean was just being kind, because that’s who he was. He hugged you because he did that. Because his daughter was your daughters best friend. Much like things were between the two of you growing up.  You couldn’t stop your thoughts from continuing. You hated when you got like this. When you let things get the better of you. You couldn’t keep going down the same jagged road. You weren’t going to heal this way. You were reopening old wounds. 

 10:07PM :  **Dean**

>>Ella is fast asleep in Mary’s room. She wanted me to tell you goodnight for her. She misses you.

10:08pm :  **You**

>>I miss her too. Thank you for letting me know, and for taking care of her. Night De.

10:09pm :  **Dean**

>> You heading to bed now?

10:09pm :  **You**

>> planning on it. Tired and had a long day, as ya know :) you heading to bed too?

10:10pm :  **Dean**

>> yeah probably. For the record, I’m excited to be spending time with you tomorrow on our half date. I’ve missed you.

10:12pm :  **You**

>> I’ve missed you. See you tomorrow, De. Sweet dreams.

10:13pm :  **Dean**

>>sweet dreams. Night Y/N.

  The last thought you had before you went to sleep was the fact that Dean Winchester really did miss you. That thought alone put a smile on your face.

**Notes for the Chapter:**

> Feedback is greatly appreciated!


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